Enantioselective direct α-amination of aldehydes via a photoredox mechanism: A strategy for asymmetric amine fragment coupling

Giuseppe Cecere, Christian M. König, Jennifer L. Alleva, David W.C. MacMillan

Research output: Contribution to journalArticle

143 Scopus citations

Abstract

The direct, asymmetric α-amination of aldehydes has been accomplished via a combination of photoredox and organocatalysis. Photon-generated N-centered radicals undergo enantioselective α-addition to catalytically formed chiral enamines to directly produce stable α-amino aldehyde adducts bearing synthetically useful amine substitution patterns. Incorporation of a photolabile group on the amine precursor obviates the need to employ a photoredox catalyst in this transformation. Importantly, this photoinduced transformation allows direct and enantioselective access to α-amino aldehyde products that do not require postreaction manipulation.

Original languageEnglish (US)
Pages (from-to)11521-11524
Number of pages4
JournalJournal of the American Chemical Society
Volume135
Issue number31
DOIs
StatePublished - Aug 7 2013

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Fingerprint Dive into the research topics of 'Enantioselective direct α-amination of aldehydes via a photoredox mechanism: A strategy for asymmetric amine fragment coupling'. Together they form a unique fingerprint.

  • Cite this